Synthetic and 1 H and 13 C NMR Spectral Studies on N-(Mono-substitutedphenyl)-acetamides H 4. NH-CO- CH 3 i. ; X = Cl, CH 3

Size: px
Start display at page:

Download "Synthetic and 1 H and 13 C NMR Spectral Studies on N-(Mono-substitutedphenyl)-acetamides H 4. NH-CO- CH 3 i. ; X = Cl, CH 3"

Transcription

1 Synthetic and 1 H and 13 C NMR Spectral Studies on N-(Mono-substitutedphenyl)-acetamides and Substituted Acetamides, 2/3/4-YC 6 H 4 NH-CO- CH 3 i X i (Y=CH 3, F, Cl, Br, NO 2 ; X = Cl, CH 3 ; i =0,1,2,3) Basavalinganadoddy Thimme Gowda, Shilpa, and Jayalakshmi K. Lakshmipathy Department of Post-Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangotri , Mangalore, India Reprint requests to Prof. B. T. G.; Fax: ; gowdabt@yahoo.com Z. Naturforsch. 61a, (2006); received July 19, 2006 Nineteen N-(2/3/4-methyl/halo/nitro-phenyl)-acetamides and substituted acetamides, 2/3/4- YC 6 H 4 NH- (Y=CH 3, F, Cl, Br or NO 2 ;X=ClorCH 3 and i =0,1,2or3),have been prepared, characterized, and their 1 H and 13 C NMR spectra in solution measured and correlated. 1 H and 13 C NMR chemical shifts were assigned to the protons and carbon atoms, respectively, in line with those for similar compounds. Since the chemical shifts are dependent on the electron density around the nucleus or associated with the atom to which it is bound, the incremental shifts of the aromatic protons or carbon atoms due to -NH- and (X = Cl or CH 3 and i =0,1,2,3)inalltheN-phenyl-substituted acetamides, C 6 H 5 NH-, are calculated by comparing the proton or carbon chemical shifts of these compounds with those of benzene or aniline. The incremental shifts due to the groups in the parent compounds have also been computed by comparing the chemical shifts of the protons or carbon atoms in these compounds with those of benzene or aniline, respectively. The computed incremental shifts and other data were used to calculate the 1 H and 13 C NMR chemical shifts of the substituted compounds in three different ways. The calculated chemical shifts by the three methods compared well with each other and with the observed chemical shifts, testing the validity of the principle of additivity of the substituent effects in these compounds. The variation of 1 H NMR chemical shifts of either the aromatic or N-H protons, with the substituents in N-(phenyl)- and N-(2/3/4-chloro/methylphenyl)-acetamides and substituted acetamides did not follow the same trend, while the variation of the 13 C NMR chemical shifts of C-1 and C=O carbon atoms and those of alkyl carbon atoms of these compounds followed more or less the same trend. Key words: 1 H and 13 C NMR Spectra; N-Aryl-acetamides; N-Aryl-substituted Acetamides. 1. Introduction The amide moiety is an important constituent of many biologically significant compounds [1]. Thus an understanding of the formation, properties and reactions of amides is central to future development in such areas as polypeptide and protein chemistry. Many imides, hydroxamic acids and hydrazides exhibit pharmacological activity, which has further stimulated recent interest in their chemistry. Further, many acetanilides exhibit fungicidal, herbicidal and pharmacological activities. We have recently reported the infrared, Raman [2], NMR [3] and NQR [4] spectra and crystal structures [5] of several N-(aryl)-acetamides and substituted acetamides. As part of these efforts of correlating spectroscopic parameters with the chem- ical bond parameters, amides of the formulae 2/3/4- YC 6 H 4 NH- (Y = CH 3, F, Cl, Br or NO 2 ; X=ClorCH 3 and i = 0, 1, 2 or 3) have been prepared, characterized, their NMR spectra measured in solution and correlated. 2. Experimental 2.1. Materials and Methods N-Phenyl- and N-(2/3/4-methyl/halo/nitro-phenyl)- acetamides/substituted acetamides of the general formulae C 6 H 5 NH- and 2/3/4-YC 6 H 4 NH- (where Y = CH 3, F, Cl, Br or NO 2 ;X= Cl or CH 3 and i = 0, 1, 2 or 3) (Table 1) were prepared from substituted anilines, substituted acetic acids (Aldrich, Germany) and thionyl chloride [2 7] / 06 / $ c 2006 Verlag der Zeitschrift für Naturforschung, Tübingen

2 596 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides Table 1. Melting points (M. p.) and N-H and C=O infrared absorption frequencies of N-(substituted-phenyl)-substituted acetamides, j-yc 6 H 4 NH-. j-y, CH 3 i X i Compound M. p. ( C) γ N H (str) (cm 1 ) γ C=O (str) (cm 1 ) 2-NO 2,CH 3 N-(2-Nitrophenyl)-acetamide s s 3-NO 2,CH 3 N-(3-Nitrophenyl)-acetamide s s 4-NO 2,CH 3 N-(4-Nitrophenyl)-acetamide s s 4-F, CH 3 N-(4-Fluorophenyl)-acetamide s s 4-Br, CH 3 N-(4-Bromophenyl)-acetamide s s 3-Cl, CH 3 N-(3-Chlorophenyl)-acetamide s s 3-Cl, CH 2 Cl N-(3-Chlorophenyl)-2-chloroacetamide s s 3-Cl, CHCl 2 N-(3-Chlorolphenyl)-2,2-dichloroacetamide s s 3-Cl, CCl 3 N-(3-Chlorolphenyl)-2,2,2-trichloroacetamide s s 3-Cl, CH 2 CH 3 N-(3-Chlorophenyl)-2-methylacetamide s s 3-Cl, CH(CH 3 ) 2 N-(3-Chlorophenyl)-2,2-dimethylacetamide s s 3-Cl, C(CH 3 ) 3 N-(3-Chlorophenyl)-2,2,2-trimethylacetamide s s 3-CH 3,CH 3 N-(3-Methylphenyl)-acetamide s s 3-CH 3,CH 2 Cl N-(3-Methylphenyl)-2-chloroacetamide s s 3-CH 3, CHCl 2 N-(3-Methylphenyl)-2,2-dichloroacetamide s s 3-CH 3, CCl 3 N-(3-Methylphenyl)-2,2,2-trichloroacetamide s s 3-CH 3,CH 2 CH 3 N-(3-Methylphenyl)-2-methylacetamide s s 3-CH 3, CH(CH 3 ) 2 N-(3-Methylphenyl)-2,2-dimethylacetamide s s 3-CH 3, C(CH 3 ) 3 N-(3-Methylphenyl)-2,2,2-trimethylacetamide s s s, Strong. Table 2. 1 H NMR chemical shifts (δ, ppm) of various aromatic and other protons in N-(3-chloro-/3-methyl-phenyl)- substituted acetamides, 3-Cl/3-CH 3 C 6 H 4 NH-. H-2 H-4 H-5 H-6 N-H Alkyl H 3-ClC 6 H 4 NH- CO-CH d 7.04d 7.17t 7.66s CO-CH 2 Cl 7.59s 7.23d 7.27d 7.62d CO-CHCl m 7.14m 7.25t 7.64t CO-CCl s 7.29s 7.31s 7.70s 10.4 CO-CH 2 CH d 7.03d 7.17t 7.65s , 1.20 CO-CH(CH 3 ) d 7.03d 7.16t 7.68s , 1.20 CO-C(CH 3 ) d 7.00d 7.13t 7.65s H CH 3 C 6 H 4 NH- CO-CH t 6.89d 7.15t 7.34s , 2.09 CO-CH 2 Cl 7.21s 6.95d 7.17d 7.32t , 4.11 CO-CHCl t 6.95s 6.98s 7.35d , 6.27 CO-CCl s 7.03d 7.26m 7.39d CO-CH 2 CH s 6.87d 7.14t 7.34d , 2.22, 1.18 CO-CH(CH 3 ) t 6.89d 7.16t 7.41s , 2.21, 1.21 CO-C(CH 3 ) d 6.87d 7.14t 7.41s , 1.27 H The commercial anilines (Sisco Research Laboratories, India) were purified by either double distillation or zone refining. All other reagents employed in the preparations and purification of reagents were of analytical grade. Pure samples of the respective anilines (aniline, 2-methylaniline, 2-chloroaniline, 2- nitroaniline, 3-methylaniline, 3-chloroaniline, 3-nitroaniline, 4-methylaniline, 4-fluoroaniline, 4-chloroaniline, 4-bromoaniline or 4-nitroaniline) were treated Table 3. 1 H NMR chemical shifts (δ, ppm) of various aromatic and other protons in N-(substituted-phenyl)- acetamides, j-yc 6 H 4 NH-CO-CH 3. j-y H-2 H-3 H-4 H-5 H-6 N-H Alkyl H 2-Cl [3] 7.30d 7.16t 7.17d 8.10d Cl 7.33d 7.04d 7.17t 7.66s Cl [3] 7.58d 7.22d 7.22d 7.58d CH 3 [3] 7.22d 7.10t 7.00t 7.54d , CH t 6.89d 7.15t 7.34s , CH 3 [3] 7.39d 7.06d 7.06d 7.39d , NO d 7.15t 7.61t 8.16d NO d 8.17m 7.16m 7.63m NO m 8.13m 8.13m 7.82m F 7.45m 6.97m 6.97m 7.45m Br 7.42d 7.26s 7.26s 7.42d Table 4. 1 H NMR chemical shifts (δ, ppm) of various aromatic and other protons in N-(phenyl)-substituted acetamides, C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1, 2, 3). H-2,6 H-3,5 H-4 N-H Alkyl H CO-CH d 7.20t 7.02t CO-CH 2 Cl 7.47d 7.27t 7.10t CO-CHCl d 7.32t 7.17t CO-CCl d 7.33t 7.18t 8.48 CO-CH 2 CH d 7.22t , 1.15 CO-CH(CH 3 ) d 7.26t 7.06t , 1.20 CO-C(CH 3 ) d 7.22t 7.01t H with mixtures of respective acetic acids (acetic acid, 2-chloroacetic acid, 2,2-dichloroacetic acid, 2,2,2-tri-

3 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides 597 NH- H-2,6 H-3,5 H-4 COCH 3 i X i H-2,6 H-3,5 H-4 NH-CO-CH CO-CH NH-CO-CH 2 Cl CO-CH 2 Cl NH-CO-CHCl CO-CHCl NH-CO-CCl CO-CCl NH-CO-CH 2 CH CO-CH 2 CH NH-CO-CH(CH 3 ) CO-CH(CH 3 ) NH-CO-C(CH 3 ) CO-C(CH 3 ) Table 5. The incremental chemical shifts (δ, ppm) of aromatic protons due to the groups NH- and - in C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1,2,3). chloroacetic acid, 2-methylacetic acid, 2,2-dimethylacetic acid or 2,2,2-trimethylacetic acid) and thionyl chloride with constant stirring. The resulting mixtures were slowly warmed to expel HCl. Excess thionyl chloride was hydrolyzed by adding cold water dropwise under ice cold conditions. The solids separated were filtered under suction, washed thoroughly with water and dried. N-Phenyl- and N-(2/3/4- methyl/halo/nitro-phenyl)-acetamides/substituted acetamides could also be prepared by treating the respective anilines with the corresponding chloroacetyl chlorides in acetone or benzene. HCl produced was removed by treating with 2 M NaOH. The N-aryl-substituted acetamides thus prepared were recrystallized from ethanol several times to constant melting points. The compounds have been characterized by determining their melting points and by recording their infrared spectra and comparing with the literature values (Table 1) Spectral Measurements The 1 H and 13 C NMR spectra of all the N-(2/3/4- methyl/halo/nitro-phenyl)-acetamides and substituted acetamides were measured on a BRUKER Ac 300F, 300 MHz FT-NMR spectrometer. The spectra were recorded in CDCl 3 and DMSO with tetramethylsilane [(CH 3 ) 4 Si] as internal standard. 3. Results and Discussion H NMR Spectra 1 H NMR chemical shifts of aromatic and alkyl protons of all the N-(2/3/4-methyl/halo/nitro-phenyl)- acetamides and substituted acetamides are shown in Tables 2 4. The various chemical shifts were assigned to the protons in line with those for similar compounds [3]. Since the chemical shift depends on the electron density around the nucleus or associated with the atom to which it is bound, the incremental shifts of the aromatic protons (ppm) due to -NH-CO- CH 3 i X i (where X = Cl or CH 3 and i =0,1,2,3) in all the N-phenyl-substituted acetamides, C 6 H 5 NH-, were computed by comparing the proton chemical shifts of these compounds (Table 4) [3] with those of the benzene proton value of 7.27 ppm (Table 5). Similarly, the incremental shifts of the aromatic protons (ppm) due to (where X = Cl or CH 3 and i = 0, 1, 2 or 3) of these compounds were also computed by comparing their proton chemical shifts with those of the aniline proton values of H-2,6 = 6.48 ppm, H-3,5 = 7.05 ppm, H-4 = 6.67 ppm (Table 5). The chemical shifts of all the aromatic protons in all the N-(2/3/4-methyl/halo/nitro-phenyl)-acetamides and substituted acetamides, 2/3/4-YC 6 H 4 NH-CO- CH 3 i X i (where Y = CH 3, F, Cl, Br or NO 2 ;X=Cl or CH 3 and i = 0, 1, 2 or 3) were then calculated in three ways by adding either the substituent contributions [8] to the corresponding 1 H NMR chemical shifts of N-phenyl-substituted acetamides (Table 4) [3] or by adding the incremental shifts due to NH- or groups (Table 5) to the 1 H NMR chemical shifts of protons of the corresponding substituted benzenes or anilines, respectively. The calculated chemical shifts by the three procedures of calculation (values not shown) led to almost the same values and were in good agreement with the experimental chemical shifts, indicating that the validity of the principle of additivity of the substituent effects is quite good with these compounds C NMR Spectra The measured 13 C NMR chemical shifts of the aromatic and alkyl carbon atoms of all the N-(2/3/4- methyl/halo/nitro-phenyl)-acetamides and substituted acetamides are shown in Tables 6 8. The various chemical shifts are assigned to the different carbon atoms in the benzene rings in conformity with the literature for similar compounds [2, 3]. The 13 C NMR

4 598 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides 3-ClC 6 H 4 NH- (X = Cl, CH 3 ; i =0,1,2,3) C-1 C-2 C-3 C-4 C-5 C-6 C=O Alkyl C CO-CH CO-CH 2 Cl CO-CHCl CO-CCl CO-CH 2 CH , 9.6 CO-CH(CH 3 ) , 19.5 CO-C(CH 3 ) , 27.3 H CH 3 C 6 H 4 NH- (X = Cl, CH 3 ; i =0,1,2,3) CO-CH , 21.4 CO-CH 2 Cl , 21.3 CO-CHCl , 21.3 CO-CCl , 21.4 CO-CH 2 CH , 21.3, 9.7 CO-CH(CH 3 ) , 21.4, 19.6 CO-C(CH 3 ) , 27.4, 21.3 H Table C NMR chemical shifts (δ, ppm) of N-(3- chloro-phenyl)-substituted acetamides. Table C NMR chemical shifts (δ, ppm) of N-(substituted-phenyl)-acetamides, j-yc 6 H 4 NH-CO-CH 3. j-y C-1 C-2 C-3 C-4 C-5 C-6 C=O Alkyl C 2-Cl [3] Cl Cl [3] CH 3 [3] , CH , CH 3 [3] , NO NO NO Br F chemical shifts of benzene, substituted benzenes, aniline and substituted anilines were also measured under identical conditions and data used for computation of incremental shifts. The incremental shifts of the aromatic carbon atoms (ppm) due to NH- (where X = Cl or CH 3 and i = 0, 1, 2 or 3) groups were computed by comparing the 13 C NMR chemical shifts of N-(phenyl)- substituted acetamides, C 6 H 5 NH- (where X=ClorCH 3 and i = 0, 1, 2 or 3) [3], with the benzene carbon value of ppm (Table 9). Similarly, the incremental 13 C NMR shifts of the aromatic carbon atoms due to (where X = Cl or CH 3 and i = 0, 1, 2, 3) groups in these compounds were computed by comparing their chemical shifts with those of the aniline carbon values of C-1 = ppm, C-2,6 = ppm, C-3,5 = ppm, C-4 = ppm (Table 9). Then the 13 C NMR chemical shifts of all the aromatic carbon atoms in all the N- Table C NMR chemical shifts (δ, ppm) of N-(phenyl)- substituted acetamides, C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1,2,3). C-1 C-2,6 C-3,5 C-4 C=O Alkyl C CO-CH CO-CH 2 Cl CO-CHCl CO-CCl CO-CH 2 CH , 9.5 CO-CH(CH 3 ) , 19.6 CO-C(CH 3 ) , 27.2 H (2/3/4-methyl/halo/nitro-phenyl)-acetamides and substituted acetamides were calculated in three ways by adding either the substituent contributions [2, 3] to the 13 C NMR chemical shifts of N-(phenyl)-substituted acetamides (Table 8) or the incremental shifts due to NH- or groups (Table 9) to the 13 C NMR chemical shifts of the corresponding substituted benzenes or anilines, respectively. The calculated 13 C NMR chemical shifts by the three procedures of calculation led to almost the same values and were in good agreement with the experimental chemical shifts, indicating the validity of the principle of additivity of the substituent effects with these compounds. 4. Comparisons and Conclusions The variation of 1 H NMR chemical shifts of either the aromatic or N-H protons with the substituents in N-(phenyl)-, N-(2-chlorophenyl)-, N-(3-chlorophen-

5 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides 599 Table 9. The incremental shifts in chemical shifts of aromatic carbon atoms due to -NH- and - groups in N-(phenyl)-substituted acetamides, C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1,2,3). NH- C-1 C-2,6 C-3,5 C-4 C-1 C-2,6 C-3,5 C-4 NH-CO-CH CO-CH NH-CO-CH 2 Cl CO-CH 2 Cl NH-CO-CHCl CO-CHCl NH-CO-CCl CO-CCl NH-CO-CH 2 CH CO-CH 2 CH NH-CO-CH(CH 3 ) CO-CH(CH 3 ) NH-CO-C(CH 3 ) CO-C(CH 3 ) yl)- and N-(4-chlorophenyl)-, N-(2-methylphenyl)-, N-(3-methylphenyl)- and N-(4-methylphenyl)-acetamides and substituted acetamides did not follow the same trend, while the variation of 13 C NMR chemical shifts of C-1 carbon atoms of these compounds followed more or less the same trend. The variations of 13 C NMR chemical shifts of C=O carbon atoms and those of alkyl carbon atoms of the above compounds also followed similar trends. Acknowledgement The authors thank the Sophisticated Analytical Instrumentation Facility, Punjab University, Chandigarh , India, for the 1 H and 13 C NMR measurements. [1] J. Jabicky (Ed.), The Chemistry of Amides, Interscience, London 1970; R. Sandler and W. Karo, Organic Functional Group Preparations, Vol. 3, Academic Press, London [2] D. K. Bhat and B. T. Gowda, J. Indian Chem. Soc. 77, 279 (2000); 79, 163 (2002); B. H. A. Kumar and B. T. Gowda, J. Indian Chem. Soc. 79, 231 (2002); B. T. Gowda, K. Jyothi, K. L. Jayalakshmi, and N. Damodara, J. Indian Chem. Soc. 82, 564 (2005). [3] B. T. Gowda, K. M. Usha, and K. L. Jayalakshmi, Z. Naturforsch. 58a, 801 (2003); B. T. Gowda, K. M. Usha, and K. Jyothi, Z. Naturforsch. 59a, 69 (2004). [4] B. T. Gowda and A. Weiss, Z. Naturforsch. 49a, 695 (1994); B. T. Gowda, S. Dou, and A. Weiss, Z. Naturforsch. 51a, 627 (1996); B. T. Gowda, D. K. Bhat, H. Fuess, and A. Weiss, Z. Naturforsch. 54a, 261, 679 (1999); B. T. Gowda, B. H. A. Kumar, and H. Fuess, Z. Naturforsch. 55a, 721 (2000). [5] B. T. Gowda, S. Dou, and A. Weiss, Z. Naturforsch. 51a, 627 (1996); B. T. Gowda, H. Paulus, and H. Fuess, Z. Naturforsch. 55a, 711, 791 (2000); 56a, 386 (2001); B. T. Gowda, I. Svoboda, and H. Fuess, Z. Naturforsch. 55a, 779 (2000); 59a, 845 (2004); B. T. Gowda, K. Jyothi, H. Paulus, and H. Fuess, Z. Naturforsch. 58a, 225 (2003). [6] A. J. Hill and E. B. Kelsey, J. Am. Chem. Soc. 44, 2357 (1922). [7] W. Pies, H. Rager, and A. Weiss, Org. Magn. Reson. 3, 147 (1971). [8] R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York 1991; W. Kemp, Organic Spectroscopy, MacMillan, London 1996.

Key words: Infrared; Nuclear Magnetic Resonance; Arylsulphonamides. CH 3,5-Cl; 3-CH 3,4-Cl; 2,4-Cl 2 or 3,4-Cl 2 ). They are

Key words: Infrared; Nuclear Magnetic Resonance; Arylsulphonamides. CH 3,5-Cl; 3-CH 3,4-Cl; 2,4-Cl 2 or 3,4-Cl 2 ). They are Infrared and NMR Spectra of Arylsulphonamides, 4-X-C 6 H 4 SO 2 NH 2 and i-x, j-yc 6 H 3 SO 2 NH 2 (X ¼ H; CH 3 ;C 2 H 5 ; F; Cl; Br; I or NO 2 and i-x, j-y¼ 2,3-(CH 3 ) 2 ; 2,4-(CH 3 ) 2 ; 2,5- (CH 3

More information

Infrared and NMR ( 1 H& 13 C) Spectra of Sodium Salts of N-Bromo-Mono and Di-Substituted-Benzenesulphonamides

Infrared and NMR ( 1 H& 13 C) Spectra of Sodium Salts of N-Bromo-Mono and Di-Substituted-Benzenesulphonamides Infrared and NMR ( 1 H& 13 C) Spectra of Sodium Salts of N-Bromo-Mono and Di-Substituted-Benzenesulphonamides B. Thimme Gowda and K. M. Usha Department of Post-Graduate Studies and Research in Chemistry,

More information

Preparation of Series Schiff Bases and Studying of their Liquid Crystalline Behavior

Preparation of Series Schiff Bases and Studying of their Liquid Crystalline Behavior Preparation of Series Schiff Bases and Studying of their Liquid Crystalline Behavior Dr. Kareem Jaber 1 1 Assistant Professor, Department of Chemistry, Faculty of Science. Email: karee2000@hotmail.com

More information

Supporting Information

Supporting Information Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy

More information

SYSTEMWIDE CHEM 2425 FINAL EXAM. Department Of Physical Sciences

SYSTEMWIDE CHEM 2425 FINAL EXAM. Department Of Physical Sciences SYSTEMWIDE CHEM 2425 FINAL EXAM Department f Physical Sciences Morphine NAME: RGANIC CHEM 2425 FINAL EXAM DIRECTINS- A periodic table is attached at the end of this exam. Please answer all questions in

More information

*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3

*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3h)-one catalyzed by Graphene Oxide

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 A rare case of a dye co-crystal showing better dyeing performance Hui-Fen Qian, Yin-Ge Wang,

More information

Supplementary Material

Supplementary Material 10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination

More information

Supporting Information. Identification and synthesis of impurities formed during sertindole

Supporting Information. Identification and synthesis of impurities formed during sertindole Supporting Information Identification and synthesis of impurities formed during sertindole preparation I. V. Sunil Kumar* 1, G. S. R. Anjaneyulu 1 and V. Hima Bindu 2 for Address: 1 Research and Development

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Supporting Information Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using

More information

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric Supplementary Information for Stable Supramolecular Helical Structure of C 6 -Symmetric Hydrogen-Bonded Hexakis(phenylethynyl)benzene Derivatives with Amino Acid Pendant Groups and Their Unique Fluorescence

More information

Synthesis and Structural Studies of 3-Imino-5-Dimethylamino- 7-Aryl/Alkylimino-1,2,4,6 Thiatriazepines

Synthesis and Structural Studies of 3-Imino-5-Dimethylamino- 7-Aryl/Alkylimino-1,2,4,6 Thiatriazepines IJP Vol. 6, o,2, Mar-April 2017 I:2319-6602 M.R Ugale 1 B..Berad 2 1 Department of Applied hemistry, GHRIET, agpur, India. 2 Post Graduate Department of hemistry, RTMU, agpur, India. orresponding Author:

More information

General Papers ARKIVOC 2007 (xvi) 65-72

General Papers ARKIVOC 2007 (xvi) 65-72 Reaction of α,α-dibromoketones with 4-amino-5-mercapto-3-methyls-triazole: synthesis of some 7H-7-alkoxy-6-aryl-3-methyl-s-triazolo [3,4-b][1,3,4]thiadiazines m Prakash,* and isha harma Department of Chemistry,

More information

Supporting Information. Excited State Relaxation Dynamics of Model GFP Chromophore Analogs: Evidence for cis-trans isomerism

Supporting Information. Excited State Relaxation Dynamics of Model GFP Chromophore Analogs: Evidence for cis-trans isomerism Supporting Information Excited State Relaxation Dynamics of Model GFP Chromophore Analogs: Evidence for cis-trans isomerism Shahnawaz Rafiq, 1 Basanta Kumar Rajbongshi, 1 isanth. air, Pratik Sen,* and

More information

pyrazoles/isoxazoles library using ketene dithioacetals

pyrazoles/isoxazoles library using ketene dithioacetals Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals Mahesh M. Savant, Akshay M. Pansuriya, Chirag V. Bhuva, Naval Kapuriya, Anil S. Patel, Vipul B. Audichya,

More information

Chemical synthesis (see also reaction scheme, bold underlined numbers in this text refer to the bold underlined numbers in the scheme)

Chemical synthesis (see also reaction scheme, bold underlined numbers in this text refer to the bold underlined numbers in the scheme) Supplementary Note This section contains a detailed description of the chemical procedures and the characterization of products. The text is followed by a reaction scheme explaining the synthetic strategies

More information

Synthesis of Schiff s Base Derivatives Using Water as Solvent.(A Green Methodology)

Synthesis of Schiff s Base Derivatives Using Water as Solvent.(A Green Methodology) Synthesis of Schiff s Base Derivatives Using Water as Solvent.(A Green Methodology) Ajmal R. Bhat 1, M. Hussain Wagay 2 1,2 Department of Chemistry, Sant Baba Bhag Singh University, Jalandhar, Punjab 144030

More information

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable 1 Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable immobilized AlCl 3 on γ-al 2 O 3 SUPPLEMETARY DATA Typical Procedure to the preparation of Azides Phenyl azide Phenyl azide was

More information

Supporting Information

Supporting Information Electronic upplementary Material (EI) for rganic Chemistry rontiers. This journal is the Partner rganisations 0 upporting Information Convenient ynthesis of Pentafluoroethyl Thioethers via Catalytic andmeyer

More information

ISATIN (PER-O-ACETYL- -D- GALACTOPYRANOSYL)THIOSEMICARBAZONES

ISATIN (PER-O-ACETYL- -D- GALACTOPYRANOSYL)THIOSEMICARBAZONES ISATIN (PER--ACETYL- -D- GALACTPYRANSYL)THISEMICARBAZNES Nguyen Dinh Thanh*, Nguyen Thi Kim Giang Faculty of Chemistry, College of Science, Vietnam National University (Hanoi), 19 Le Thanh Tong, Hanoi

More information

Carboxylic Acid Derivatives. Citation University (1980), 57(5-6):

Carboxylic Acid Derivatives. Citation University (1980), 57(5-6): Preparation of 3-Aryl-2H-1,2,4-benz Titleby the Reaction of o-aminobenzenesu Carboxylic Acid Derivatives Author(s) Tanimoto, Shigeo; Yoshida, Norio; S Okano, Masaya Citation Bulletin of the Institute for

More information

Preparation, Investigation, Correlation Analysis and Theoretical Study of Bromoacetamide and Bis (2- Bromo Acetamide) Derivatives

Preparation, Investigation, Correlation Analysis and Theoretical Study of Bromoacetamide and Bis (2- Bromo Acetamide) Derivatives International Journal of Chemistry and Applications. ISSN 0974-3111 Volume 4, Number 3 (2012), pp. 205-210 International Research Publication House http://www.irphouse.com Preparation, Investigation, Correlation

More information

Supplementary Information (Manuscript C005066K)

Supplementary Information (Manuscript C005066K) Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)

More information

Accessory Information

Accessory Information Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department

More information

Supplementary Information

Supplementary Information Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)

More information

An Eco-friendly Route to Synthesis of Quinolines

An Eco-friendly Route to Synthesis of Quinolines An Eco-friendly Route to Synthesis of Quinolines A.D. Mishra Department of Chemistry, Tribhuvan University, P.N. Campus, Pokhara, Nepal E-mail: mishraad05@hotmail.com Abstract Some 2-hydroxy-4-methyl-6-

More information

Supporting Information

Supporting Information Supporting Information Nano CuFe 2 O 4 as a Magnetically Separable and Reusable Catalyst for the Synthesis of Diaryl / Aryl Alkyl Sulfides via Cross-Coupling Process under Ligand Free Conditions Kokkirala

More information

Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocylic Carbene Complexes of Rh, Ir and Pd

Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocylic Carbene Complexes of Rh, Ir and Pd J. Am. Chem. Soc. Supporting Information Page S1 Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocylic Carbene Complexes of Rh, Ir and Pd Adelina Voutchkova, Leah N. Appelhans,

More information

Supplementary Information. Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated Glycals and Sulfamate Ester

Supplementary Information. Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated Glycals and Sulfamate Ester Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supplementary Information Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated

More information

Synthesis and Computational studies of synthesized 3-(4 -Bromophenyl)-5-(aryl substituted) Isoxazole derivatives

Synthesis and Computational studies of synthesized 3-(4 -Bromophenyl)-5-(aryl substituted) Isoxazole derivatives International Journal of Chemistry and Applications. ISSN 0974-3111 Volume 5, Number 1 (2013), pp. 31-37 International Research Publication House http://www.irphouse.com Synthesis and Computational studies

More information

Pelagia Research Library

Pelagia Research Library Available online at www.pelagiaresearchlibrary.com Der Chemica Sinica, 2015, 6(7):78-86 Synthesis and structural elucidation of Famciclovir B Sudha Rani 1, Ramana Kumar Kakarla 1 * and Srilalitha Vinnakota

More information

CH 320/328 N Summer II 2018

CH 320/328 N Summer II 2018 CH 320/328 N Summer II 2018 HW 1 Multiple Choice Identify the choice that best completes the statement or answers the question. There is only one correct response for each question. (5 pts each) 1. Which

More information

Anion recognition in water by a rotaxane containing a secondary rim functionalised cyclodextrin stoppered axle

Anion recognition in water by a rotaxane containing a secondary rim functionalised cyclodextrin stoppered axle Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary Information: Anion recognition in water by a rotaxane containing a secondary rim

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,

More information

Supplementary Material. Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons

Supplementary Material. Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons Supplementary Material Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons İrfan Çapan a and Süleyman Servi b a Gazi University, Technical Sciences

More information

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted

More information

A dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex

A dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex Supporting Information (SI) A dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex Xiaoya Li, Mingming Yu, Faliu Yang, Xingjiang

More information

Supporting Information Water-soluble 1,2,4-Triazole with Diethylene Glycol Monoethyl Ether

Supporting Information Water-soluble 1,2,4-Triazole with Diethylene Glycol Monoethyl Ether Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is The Royal Society of Chemistry 2014 Supporting Information Water-soluble 1,2,4-Triazole with Diethylene

More information

CHEM 303 Organic Chemistry II Problem Set III Chapter 14 Answers

CHEM 303 Organic Chemistry II Problem Set III Chapter 14 Answers CHEM 303 rganic Chemistry II Problem Set III Chapter 14 Answers 1) Give the major products of each of the following reactions. If a mixture is expected, identify the major product. + H 3 CHC CHCH 3 H 2

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water Dong-Hwan Lee, Ji-Young Jung, and Myung-Jong

More information

Int. J. Mol. Sci. 2005, 6, International Journal of

Int. J. Mol. Sci. 2005, 6, International Journal of Int. J. Mol. Sci. 2005, 6, 11-17 International Journal of Molecular Sciences ISSN 1422-0067 2005 by MDPI www.mdpi.org/ijms/ Substituent Effects in the 13 C-NMR Spectra of Six-Membered Nitrogen Heteroaromatic

More information

Supporting Information

Supporting Information Supporting Information Efficient copper-catalyzed coupling of aryl chlorides, bromides and iodides with aqueous ammonia Hanhui Xu and Christian Wolf* Department of Chemistry, Georgetown University, Washington

More information

Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation

Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts

More information

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition

More information

Studies on Synthesis of Pyrimidine Derivatives and their Pharmacological Evaluation

Studies on Synthesis of Pyrimidine Derivatives and their Pharmacological Evaluation http://www.e-journals.net ISS: 0973-4945; CDE ECJHA E- Chemistry Vol. 4, o.1, pp 60-66, January 2007 Studies on Synthesis of Pyrimidine Derivatives and their Pharmacological Evaluation T. A. AIK and K.

More information

Catalytic Hydrogenation of Functionalized Amides Under Basic and Neutral Conditions

Catalytic Hydrogenation of Functionalized Amides Under Basic and Neutral Conditions Electronic Supplementary Material (ESI) for Catalysis Science & Technology. This journal is The Royal Society of Chemistry 2014 Supplementary Information Catalytic Hydrogenation of Functionalized Amides

More information

Preparation of Aliphatic Amines by the Leuckart Reaction

Preparation of Aliphatic Amines by the Leuckart Reaction Preparation of Aliphatic Amines by the Leuckart Reaction Lin Yang, Rongji Dai, Wei Liu and Yulin Deng, School of Life Science and Technology, Beijing Institute of Technology, 5 South Zhongguancun Street,

More information

Supplementary Information. g, 29 mmol) in absolute EtOH (25 cm 3 ) was treated with diethyl oxalate (3.86 g, 26.4

Supplementary Information. g, 29 mmol) in absolute EtOH (25 cm 3 ) was treated with diethyl oxalate (3.86 g, 26.4 Supplementary Information Synthesis of a-hydroxycinnamic acids (5) α-hydroxycinnamic acids 5a,b were commercially available and 5g was prepared by a literature procedure. 1 Ethyl 3-(4-chlorophenyl)- 3-cyano-2-oxopropanoate

More information

SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits)

SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits) SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits) This lab you can revisit the fist experiment of this quarter and synthesize more azo dyes of your choice. The old procedure is given below followed by

More information

N_HW1 N_HW1. 1. What is the purpose of the H 2 O in this sequence?

N_HW1 N_HW1. 1. What is the purpose of the H 2 O in this sequence? N_HW1 N_HW1 Multiple Choice Identify the choice that best completes the statement or answers the question. There is only one correct response for each question. 1. What is the purpose of the H 2 O in this

More information

Supporting Information

Supporting Information Supporting Information for Engineering of indole-based tethered biheterocyclic alkaloid meridianin into -carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization

More information

Supporting Information

Supporting Information Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,

More information

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins Bearing a Fused Pyrrolidine Scaffold. Dorota Kowalczyk, and Łukasz Albrecht*

Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins Bearing a Fused Pyrrolidine Scaffold. Dorota Kowalczyk, and Łukasz Albrecht* Organocatalytic Doubly Annulative Approach to 3,4-Dihydrocoumarins Bearing a Fused Pyrrolidine Scaffold Dorota Kowalczyk, and Łukasz Albrecht* Institute of Organic Chemistry, Chemistry Department, Lodz

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

Tautomerism in 1-hydroxy-2-naphthaldehyde Schiff bases: Calculation of tautomeric isomers using carbon-13 NMR

Tautomerism in 1-hydroxy-2-naphthaldehyde Schiff bases: Calculation of tautomeric isomers using carbon-13 NMR Spectroscopy 17 (2003) 747 752 747 IOS Press Tautomerism in 1-hydroxy-2-naphthaldehyde Schiff bases: Calculation of tautomeric isomers using carbon-13 NMR Salman R. Salman a and Fadhil S. Kamounah b, a

More information

Electronic Supporting Information

Electronic Supporting Information Electronic Supporting Information Reactions of Tp(NH=CPh 2 )(PPh 3 )Ru Cl with HC CPh in the presence of H 2 O: Insertion/Hydration Products Chih-Jen Cheng, a Hung-Chun Tong, a Yih-Hsing Lo,* b Po-Yo Wang,

More information

Supporting Information:

Supporting Information: Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information: A metal free reduction of aryl-n-nitrosamines to corresponding hydrazines

More information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL

More information

Electropolymerization of cobalto(5,10,15-tris(4-aminophenyl)- 20-phenylporphyrin) for electrochemical detection of antioxidant-antipyrine

Electropolymerization of cobalto(5,10,15-tris(4-aminophenyl)- 20-phenylporphyrin) for electrochemical detection of antioxidant-antipyrine Supplementary material Electropolymerization of cobalto(5,10,15-tris(4-aminophenyl)- 20-phenylporphyrin) for electrochemical detection of antioxidant-antipyrine Sambandam Anandan* a, Arumugam Manivel a,

More information

(2) After dissolving a solid in a solvent at high temperature, the solution is not filtered.

(2) After dissolving a solid in a solvent at high temperature, the solution is not filtered. Name Key 216 W13-Exam No. 1 Page 2 I. (10 points) The goal of recrystallization is to obtain purified material with a maximized recovery. For each of the following cases, indicate as to which of the two

More information

Synthesis of Organic Compounds And Study its liquid Crystalline Behavior

Synthesis of Organic Compounds And Study its liquid Crystalline Behavior Synthesis of Organic Compounds And Study its liquid Crystalline Behavior Dr. Sajida.H. Ridha and Dhia.A. Hanoush Department of Chemistry, Faculty of Education for Women., Iraq. e-mail ID: sajida-67@gmail.com

More information

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School

More information

Supporting Information for:

Supporting Information for: Supporting Information for: Photoenolization of 2-(2-Methyl Benzoyl) Benzoic Acid, Methyl Ester: The Effect of The Lifetime of the E Photoenol on the Photochemistry Armands Konosonoks, P. John Wright,

More information

Supplementary Materials. Table of contents

Supplementary Materials. Table of contents Supplementary Materials Microwave- Assisted Multicomponent Ecofriendly Synthesis of 3-Bihetaryl-2-oxindole Derivatives Grafted with Phenothiazine Moiety A. S. Al-Bogami 1 and A. S. El-Ahl 1,2 * 1 Chemistry

More information

Nanocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of N-(2- pyridyl)indoles

Nanocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of N-(2- pyridyl)indoles Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2015 Supplementary Material (ESI)

More information

Supporting Information

Supporting Information Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook

More information

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments

More information

Supporting Information for:

Supporting Information for: Supporting Information for: Equilibrium Acidities of Proline Derived Organocatalysts in DMSO Zhen Li, Xin Li,* Xiang Ni, Jin-Pei Cheng* State Key Laboratory of Elemento-Organic Chemistry, Department of

More information

Supplementary Information. Rational Design of Soluble and Clickable Polymers Prepared by. Conventional Free Radical Polymerization of

Supplementary Information. Rational Design of Soluble and Clickable Polymers Prepared by. Conventional Free Radical Polymerization of Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supplementary Information Rational Design of Soluble and Clickable Polymers Prepared by

More information

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Supporting Information Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Hua-Jin Xu, Yi Lu, *, Marcus E. Farmer, Huai-Wei Wang, Dan Zhao, Yan-Shang Kang, Wei-Yin Sun, *, Jin-Quan Yu

More information

NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY

NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY A STUDENT SHOULD BE ABLE TO: 1. Identify and explain the processes involved in proton ( 1 H) and carbon-13 ( 13 C) nuclear magnetic resonance

More information

Chapter -2. Synthesis of some novel phenyl. N-mustard quiazoline Conjugates having a urea linker

Chapter -2. Synthesis of some novel phenyl. N-mustard quiazoline Conjugates having a urea linker Chapter -2 Synthesis of some novel phenyl -mustard quiazoline Conjugates having a urea linker Synthesis of -mustard-quinazoline conjugates 2.1 Chemistry The synthesis of newly designed -mustards-quinazoline

More information

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,

More information

Supporting Information

Supporting Information 1 Supporting Information Gold-catalyzed Synthesis of 3-arylindoles via Annulation of Nitrosoarenes and Alkynes Siva Murru, August A. Gallo and Radhey S. Srivastava* Department of Chemistry, University

More information

Growth and Characterization of 4 Bromo 2-nitro Aniline a New Nonlinear Optical Organic Crystal

Growth and Characterization of 4 Bromo 2-nitro Aniline a New Nonlinear Optical Organic Crystal International Journal of Pure and Applied Physics ISSN 0973-1776 Volume 6, Number 2 (2010), pp. 151 156 Research India Publications http://www.ripublication.com/ijpap.htm Growth and Characterization of

More information

Cobalt- and Iron-Catalyzed Isomerization-Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes

Cobalt- and Iron-Catalyzed Isomerization-Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes Cobalt- and Iron-Catalyzed Isomerization-Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes Takahiko Ogawa, a Adam J. Ruddy, a Orson L. Sydora, *,b Mark

More information

Efficient Pd-Catalyzed Amination of Heteroaryl Halides

Efficient Pd-Catalyzed Amination of Heteroaryl Halides 1 Efficient Pd-Catalyzed Amination of Heteroaryl Halides Mark D. Charles, Philip Schultz, Stephen L. Buchwald* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting

More information

INTRODUCTORY ORGANIC CHEMISTRY II --- PROBLEM SET #2

INTRODUCTORY ORGANIC CHEMISTRY II --- PROBLEM SET #2 CHEM 222 Section 01 Fall 2007 Dr. C. Rogers Page 1 of 5 INTRDUCTRY RGANIC CHEMISTRY II --- PRBLEM SET #2 DISTRIBUTED: Thurs.Nov.15 th. CMPLETIN DEADLINE: Thurs.Nov.29 th @ 10:15am. INSTRUCTINS: Work through

More information

Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008

Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008 Supplementary Information for: Scrambling Reaction between Polymers Prepared by Step-growth and Chain-growth Polymerizations: Macromolecular Cross-metathesis between 1,4-Polybutadiene and Olefin-containing

More information

Halogen halogen interactions in diiodo-xylenes

Halogen halogen interactions in diiodo-xylenes Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society

More information

Supplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes

Supplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes Supplementary Material onic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes Mahboobe Nouzarian 1, Rahman Hosseinzadeh 1,*, and Hamid

More information

Supporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor

Supporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Supporting information Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Toni Mäkelä, a Elina Kalenius a and Kari Rissanen a* a University of Jyvaskyla, Department of Chemistry, Nanoscience

More information

Maksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov

Maksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov 1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv

More information

John H. MacMillan and Stephen S. Washburne. Dept of Chemistry, Temple University, Philadelphia, Pa 19122

John H. MacMillan and Stephen S. Washburne. Dept of Chemistry, Temple University, Philadelphia, Pa 19122 Further Studies of the Interaction of Carbonyl Compounds with Organometallic Azides, the Reaction of Napthoquinones with Trimethylsilyl Azide John H. MacMillan and Stephen S. Washburne Dept of Chemistry,

More information

Principles of Molecular Spectroscopy: Electromagnetic Radiation and Molecular structure. Nuclear Magnetic Resonance (NMR)

Principles of Molecular Spectroscopy: Electromagnetic Radiation and Molecular structure. Nuclear Magnetic Resonance (NMR) Principles of Molecular Spectroscopy: Electromagnetic Radiation and Molecular structure Nuclear Magnetic Resonance (NMR) !E = h" Electromagnetic radiation is absorbed when the energy of photon corresponds

More information

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and

More information

- 1/2. = kb o = hνν + 1/2. B o increasing magnetic field strength. degenerate at B o = 0

- 1/2. = kb o = hνν + 1/2. B o increasing magnetic field strength. degenerate at B o = 0 NMR EXPERIMENT When magnetically active nuclei are placed into an external magnetic field, the magnetic fields align themselves with the external field into two orientations. During the experiment, electromagnetic

More information

Supplementary Materials

Supplementary Materials Supplementary Materials ORTHOGOALLY POSITIOED DIAMIO PYRROLE- AD IMIDAZOLE- COTAIIG POLYAMIDES: SYTHESIS OF 1-(3-SUBSTITUTED-PROPYL)-4- ITROPYRROLE-2-CARBOXYLIC ACID AD 1-(3-CHLOROPROPYL)-4- ITROIMIDAZOLE-2-CARBOXYLIC

More information

7a. Structure Elucidation: IR and 13 C-NMR Spectroscopies (text , , 12.10)

7a. Structure Elucidation: IR and 13 C-NMR Spectroscopies (text , , 12.10) 2009, Department of Chemistry, The University of Western Ontario 7a.1 7a. Structure Elucidation: IR and 13 C-NMR Spectroscopies (text 11.1 11.5, 12.1 12.5, 12.10) A. Electromagnetic Radiation Energy is

More information

Unit 13-NITROGEN CONTAINING ORGANIC COMPOUNDS

Unit 13-NITROGEN CONTAINING ORGANIC COMPOUNDS Unit 13-NITROGEN CONTAINING ORGANIC COMPOUNDS Two marks: 1. Name the product obtained when a nitrile is reduced by H 2 /Ni,. Give the equation. H 2 /Ni, Primary amine: RCN RCH 2 NH 2. 2. How is nitrobenzene

More information

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro

More information

SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits)

SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits) SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits) This lab you can revisit the fist experiment of this quarter and synthesize more azo dyes of your choice. The old procedure is given below followed by

More information

Supplementary Information for. Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO-NHOH) to anilines

Supplementary Information for. Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO-NHOH) to anilines Supplementary Information for Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO-NHOH) to anilines Yujiro Hoshino,* a Moriaki Okuno, a Eri Kawamura, a Kiyoshi Honda, b and Seiichi Inoue

More information

CHEM Chapter 13. Nuclear Magnetic Spectroscopy (Homework) W

CHEM Chapter 13. Nuclear Magnetic Spectroscopy (Homework) W CHEM 2423. Chapter 13. Nuclear Magnetic Spectroscopy (Homework) W Short Answer 1. For a nucleus to exhibit the nuclear magnetic resonance phenomenon, it must be magnetic. Magnetic nuclei include: a. all

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION Z. Anorg. Allg. Chem. 2016 ISSN 0044 2313 SUPPORTING INFORMATION Title: Lanthanides Mediated Oxidative Cross Coupling of Benzylalcohols and Various Amines to Form Corresponding Imines Author(s): J. Bhattacharjee,

More information

4.1 1-acryloyl-3-methyl-2,6-bis(3,4,5-trimethoxy phenyl)piperidine-4-one (1)

4.1 1-acryloyl-3-methyl-2,6-bis(3,4,5-trimethoxy phenyl)piperidine-4-one (1) 4 Piperidine derivatives 4.1 1-acryloyl-3-methyl-2,6-bis(3,4,5-trimethoxy phenyl)piperidine-4-one (1) 4.1.1 Synthesis To a well stirred solution of 3-methyl-2,6-bis(3,4,5-trimethoxyphenyl)piperi dine-4-one

More information